This is Thanksgiving week in America, a time when families gather around traditional meals and enjoy the chance to reflect on all that they are thankful for. But not without a few awkward exchanges, I’m sure. There is a rash of articles every year with tips and tricks on how to avoid politics or finances or love or health or practically any other topic worth discussing with your loved ones.

The fact that we write and read such articles feels very strange. We clearly have some tension among us.

SNL touched on this with a great skit from a few years ago. A family gathers and immediately gets mired in the hardship of different opinions, beliefs, and preferences. There’s the usual passive-aggressive sniping over politics, religion, and much more. A child sits at the end of the table, exasperated at how these adults can get so worked up over nothing, and then somehow finds the last remaining boombox of the modern era and uses it to rescue the group. She presses Play and the music starts. Suddenly, through the Power Of Adele, the family transforms—in more ways than one. It’s funny stuff.

I would never consider the holiday dinner table to be the best place for a difficult conversation. All the same, this week’s book feels all the more topical given the time of year. Difficult Conversations is a bestselling business book published in 1999 by Harvard Law School professors Douglas Stone, Bruce Patton, and Sheila Heen. Their photo in the original hardback is one of the most 90’s-perfect things I’ve ever seen. Look at this. It’s so perfectly orchestrated.

Behold the perfect representation of the dust cover author photo from the 1990s.

Stone and Patton are holding their suit jackets over their shoulder. They’re casual yet serious. And Heen is right there in the middle, leveling you with a gaze that makes her the Elaine to their Jerry and George.

Tepid jokes aside, they provide us some great work here. The book stems from the work of the Harvard Negotiation Project, the same group that produced the classic Getting To Yes. When combined with the lesser-known-but-equally-great Bargaining for Advantage, you have a fantastic trilogy on the topic. Out of all three, Difficult Conversations has always had the broadest applicability to work and home. I think it’s the best one to read first.

Difficult Conversation – Antifragile?

We avoid difficult conversations. Yet, I can’t think of anything else that has improved my circumstances more. Difficult conversations bridge the trenches we build around our self-interests, allowing us to confront the people and issues we otherwise try to insulate ourselves from. In every single circumstance that I have engaged in a difficult conversation, I have walked away with more information, more understanding, and more growth. I do not use the term lightly but I think that the pressure and pain of these conversations has that rare “antifragile” quality that actually makes us stronger. So if you are like me and you want to continually improve, engage in these conversations wherever you find the resistance. You’ll be the life of the party, I’m sure!

Once you have the necessary tools, that is.

I learned some of these tools from education. It is an incredibly rich field for learning how to make connection. It has to be. Teachers understand they’re working with children; the rest of us tend to forget that we work with children, too. They just masquerade in adult bodies.

So how do we break through? How do we deliver difficult-but-necessary messages to those who are emotionally fragile? How do we avoid the trap of fragility ourselves? There is something you want to say to someone here and now. And someone wants to say something to you, too. If we can do this right, we can grow. All of us.

Don’t Wait To Deliver The Message

Here’s a great line from our book:

Choosing not to deliver a difficult message is like hanging on to a hand grenade once you’ve pulled the pin.

I’ve held many such grenades. It is something of a biological family tradition to withhold feelings, thoughts, and opinions. All in the name of conflict avoidance. Better to just say nothing. The silence can be seen as beneficent tolerance. Or we could just call it lily-livered passive aggressiveness. Take your pick.

Anyway, my greatest weakness as a leader and manager is my inability to confront situations and deliver difficult messages in the moment. When I’m at my weakest point, I let things simmer for a while. I look for patterns. Is there an issue among the team? A failing I want to correct? Bad behavior? I note it and put it in the catalog, carefully tagged for easy retrieval. Later, when there is a critical mass of such things, I bring it to the person’s attention. I deliver a carefully-constructed, well-reasoned message with a record and history that runs pretty deep. It’s an oral recitation of all the bad things that have brought us to that particular point. And even though this message is hand-crafted to be as diplomatic and gentle and caring as possible, it inadvertently overwhelms the person. I’ve heard these words more than once: “I had no idea you felt this way.”

Sound familiar?

I’ve had a very good and talented person tell me to just tell them what I think in the moment. I have a hard time with that. The internal struggle comes from the fact that we, collectively, only see conversations as either good, fun things or heated arguments. As always, it’s the dichotomous thinking of the beginner that gets us every time.

But there’s another part to this, too. To circle back to our quote, consider the language one more time:

Choosing not to deliver a difficult message is like hanging on to a hand grenade once you’ve pulled the pin.

The greatest problem is the fact that we consider our job to be the successful delivery of a message.

Stop delivering messages. Engage in a conversation instead.

A brilliant line that hits me square in the gut follows:

Coated with sugar, thrown hard or soft, a hand grenade is still going to do damage. Try as you may, there’s no way to throw a hand grenade with tact or outrun the consequences.

Why do I have this tendency to bottle up the issues? To catalog them and deliver a carefully-crafted message? To wait until there is critical mass? There are two reasons.

First, I’m a nice person who is deathly afraid of “over-management” and operates in a very relativistic mode. I’m always trying to find the middle ground between a spineless jellyfish and an absolute brick wall. So I struggle with correction because I’m often unsure it’s justified. How do I know this is a real issue? How can I be sure that it won’t take care of itself without my intervention? Do I need to spend capital on this or do I wait for something else? This is unrelated to our topic so we’ll save it for later weeks.

Second, I’m a native Southerner steeped in the long tradition of diplomatic understatement. There’s nothing so eloquent as an indirect criticism. Or a direct delivery of compassion wrapped around a hard nugget of truth. This is referred to as “Build-Break-Build” in the realm of constructive feedback. “Hey employee. You’re really good at X but you did Y, which isn’t good, but you’re also good at Z so please do that and keep up the good work.” See what happened there? A small bit of correction was wrapped in a genuine-but-sugary-sweet package of praise.

It’s effective but it’s a trick. Such tricks don’t work for long because they are geared toward a message and not a conversation. The first few pages of this excellent book explains why we must move from messages (i.e. hand grenades) to conversations instead. Specifically, learning conversations. The best kind.

All my success and progress, on personal and professional fronts, can be attributed to such conversations. They are difficult. Most worthy things are. We can get even better at them. Doing so creates a ratchet, a good thing that makes more good things, in a nice, reinforcing way. It’s the sort of feedback loop (borrowing from last week’s systems thinking) we all need.